He was a founding partner of Cutler & Stanfield LLP, which became the second largest environmental law firm in the country, eventually merging that practice with international firm Akin Gump in 2000.[5]

Cutler resides in Cape Elizabeth with his wife, Melanie Stewart Cutler. They have two adult children.[6]

2010 Gubernatorial campaign

On December 9, 2009, Cutler officially launched his campaign for governor of Maine. Had he been elected, he would have been Maine’s third Independent governor. He was endorsed by Maine's second Independent governor, Angus King.[7]

In a close election night race, Cutler took an early lead.[8] As the results came in from Maine's smaller and more rural communities, Cutler's lead shrank, and eventually opponent Paul LePage took the lead. Based on early, unofficial results, the Bangor Daily News projected that LePage would win, and Cutler conceded on the morning after the election.[9]

2014 Gubernatorial campaign

On June 6, 2013, Cutler announced on radio station WGAN's morning show that he would again run for governor, with a formal announcement coming after Labor Day. He dismissed the suggestion that his candidacy would result in another LePage victory, stating that he wouldn't run if he didn't think he could win.[10] While he was again endorsed by Angus King on August 18, 2014 [11] King withdrew his endorsement on October 29, 2014 in favor of the Democratic Party candidate, Mike Michaud.[12]

Cutler finished a distant third, with LePage winning reelection. Though many Democrats believe that Cutler was a two-time spoiler, it is a label he and his supporters reject.[13]